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Publication numberUS2211001 A
Publication typeGrant
Publication dateAug 13, 1940
Filing dateMar 10, 1938
Priority dateMar 18, 1937
Publication numberUS 2211001 A, US 2211001A, US-A-2211001, US2211001 A, US2211001A
InventorsChwala August
Original AssigneeGen Aniline & Film Corp
Export CitationBiBTeX, EndNote, RefMan
External Links: USPTO, USPTO Assignment, Espacenet
Oxalkyl derivatives of imidazolines
US 2211001 A
Abstract  available in
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Claims  available in
Description  (OCR text may contain errors)

Patented Aug. 13, 1940 mesne assignments, to General Aniline & Film Corporation, New York, N. ,Y., a corporation of Delaware No Drawing. Application March 10, 1938, Se-

n! Uni-m:

to the manufacture of such products and especially to the condensation of cyclic amidines, derived from aliphatic diamines with an alkylene 5 oxide or a monohalogen derivative of a polyhydric alcohol. I

I have found that cyclic acid amidines derived from .aliph'atic diamines, for instance imidazollines and tetrahydropyrimidines, and containing exchangeable hydrogen atoms, for instance, imido. amido or hydroxyl groups, may be condensed with a LZ-alkgdene oxide, such as ethylene oxide,

propylene oxide, 8 H hut lene oxide, cyclofurthermoraisteriflcation witmpciyahasieninan hexene oxide, epichlorihydrin, side chains mix such as, for instance, sulfuric acidether-alcohol groups being, thereby, introduced into the molecule of these amidines. The reaction may be performed, if desired, in the presence of a catalyst such as sodium hydroxide, potassium hydroxide orv sodium methylate or of an acid substance, for instance sodium bisulfate at a raised temperaturewhereby one or several mols of the alkylene oxide may enter into reaction. Instead of the 1.2-alkylene oxide, there may also be used amonohalogen derivative of polyhydric alcohols, for instance, glycol, diglycol,

polygiycol, glycerol, polyglycerol.

These compounds are caused to act upon the cyclic acid amidine at a raised temperature and, if desired, under pressure. The reaction may also '30 be performed several times, byconverting, for

instance, an imidazoline containing the group by means of metallic sodium into the sodium compound and causing the lat- .ter to react with the halogen compound of a polyhydric alcohol at a raised temperature and in the presence of an inert solvent. It is also possible to react the compounds obtainable from cyclic 'amidines and halogen derivatives of a polyhydric alcohol and containing one or several hydroxyl. groupswith alkylene oxldes..-

By the introduction of the ether-alcohol side chains the properties of the cyclic acid amidines may be. influenced-and the solubility, especially of the high-"molecular compounds, may be improved which renders them considerably more useful, for instance, as textile or leather adjuvants. t l The condensation products are oily to fator wax-like products whose solubility in water varies according to the number of the alkyleneoxy groups.

In case the reaction products are insoluble in water or are soluble in water only to a small extent they may be rendered water-soluble by reaction of their nitrogen group or free OI-I- rial No. 195,118. In Austria March 18, 1937 (Cl. 260-309) This invention relates to cyclic amidines and groups which may also be present in the form of alkali alcholates with reactive compounds, such as sulfuric acid chlorosulfonic acid or chloroacetic acid The subsequent reaction at the groups mentioned may also be performed in ors der to vary the effect of the products.

As such reactions there may be mentioned, for instance, the reaction with halogen-cairboxylic acids containing a reactive halogen atom, with haiogen-alkylsulfonic acids containing a reactive to halogen atom, with di-v or poly-basic carboxylic acids with formation of acid esters of these acids:

or phosphoric acid. The hydroxyl group may 18 also be esterified, for instance, with hydrochloric acid, with organic carboxylic or sulionic acids; furthermore, by treatment with phosgenc with formation of. chloro-carbonic acid ester; also by the action of formaldehyde and HCl the go omega-chloromethyl others may be obtained. and these products may be subjected to further reactions, the halogen compound obtainable from a compound which contains an OH-group and in which OH has been exchanged for C1 or ob- 25 tainable from the action of CHaO and HCl ma be caused to react with potassium cyanide and the reaction product may be saponifiedsubsequently or a chlorocarbonic acid ester obtainable by treatment 'of a compound, containing an OK: 30 group with phosgene may. be caused to react with hydroxy-alkyl-sulfonic acids, aminoalkylsulfonic acids, aminoaryl-sulfonic acids, aminoalkyloraminoaryl-carboxylic acids. The said reaction products are in part oily bodies and, in a; Part bodies of a fats-V to wax-"or resin-like naturei theymay also be obtained as a solid pulverizable mass. Insofar as they contain hydro philic groups, they are generally water-soluble.

But there are also obtained water-insoluble prod- 49/ My The new products are very suitable for use in the, textile, leather and dyeing industry. They are used for washing crude textile materials as well as finished textiles from natural or arti- 5 ficial textile materials or for washing skins and feathers for' beds. Also in the so-called dry washingprocess the new products may be used with a good result in combination with organic solvents. Furthermore, they are used for greas- 50 ingwool, particularly in combination with a min 'eral oil or olein, as emulsifying and dispersing agents for all purposes in the textile and'dyeing 1 industry. 'They are, furthermore, very good wetting and penetrating agents.

ndensing them with monohalogen derivatives of polyhy i a s Q e -undecyl-N -(dihyof undecylimidazoline heated to 120 0-140 0.,

until the increase in weight amounts to about 2 mols of ethylene oxide, calculated upon one mol of the base.

A light-brownish, viscous mass is obtained l5 which easily and entirely dissolves in water to a clear solution. I ts agueQus solatio oams on contain alcoholic or phenolic hydroxyl groups ordfiamino-radicals. -undecyl-N-(aminoethyll imidazoline:


OiiHn.CN-CH2 V 26 4: it?

man/tor instance, be caused to react with 2 mols of ethylene oxide with formation of CHLCHI-NB-ClHlbzCzHl-OH rz-cm Cn'HimC N-CHi I In the case of pentadecyl-N-ethyl-hydroxy-tetra- I hydropyrimidine:

Ci s I l CH:

cameo 011(011) NCHI the ethylene oxide is added at the hydroxyl group. The hydroxyl groups may also be present in the carbon chain, for instance, in imidazolines which are derived from castor oil fatty acid. The abovenamed cyclic acid amidines may contain, besides i the imino-, aminoor hydroxyl-groups, other radicals, especially sulfonic acid groups. By introducing ether-alcohol groups the sulfonic acids of high-molecular, imidazolines or tetrahydropyrimidines may be rendered soluble in dilute acids in which otherwise they are hardly soluble.

Ether-alcohol groups may also be introduced into imidazolines or tetrahydropyrimidines by 55 droxypropyl) -imidazoline:

' omomomcmon -om R in.-- guns \T- H: for instance, may be caused to react, while heating, with glycerol-monochlorhydrin, an ether being formed.

It is also possible to condense with imidasolines or tetrahydropyrimidines monohalogen derivatives of ether-alcohols, such as for instance, monochloro-diglycol ether,

ClCHs--CH:CHa-'-CH :OH or monohalogen derivatives 01 poly'glycerols such as may be formed by the action of hydrogen chloride upon polyglyl ierols.

Suitable starting materials for hardened casfor oil and'trimethylen 1 and 13 parts of bensyl chloride are, by heating at hydroxyheptadecyl tetrahydropyrimidine.

the present process are imidanolines and, tetrahydropyrimi-- (2) In the manner described in Example 1, 306 parts of heptadecenyl-imidazoline are condensed with propylene oxide by introducing the latter, drop by drop, into the molten base, at a temperature 'of 120 C.--140 C. As soon as about 4 mols of propylene oxide-calculated upon the weight of the tree base- -have been adsorbed, the introduction of propylene oxide is interrupted.

A brownish mass is obtained which dissolves in water .to a clear solution, while strongly foaming.

(3) Heptadecyl-tetrahydropyrimidine is; in the manner described in Example 1, condensed with 0 ethylene oxide, until the i'n amounts to .8 mole of ethylene oxide, calculated upon the weight of the EBSCfiUSGd. A brown, liquid mass is obtained which easily dissolves in water, while foaming. (4) 111 parts of heptadecenyl-imidazoline are condensed with 116 parts of finely pulverized sodium gamma-chloro-beta-hydroxypropane-sulionate of about 92 per cent. strength, by heating at 160 C.-180f C. Ethylene oxide is, at 120 C.- 140 0., introduced into the melt obtained, until the increase in weight amounts to 3-5 mols of ethylene oxide, calculated upon hepta-decenylimidazoline-hydroxy-propane-sulfonic acid.

The product obtained dissolves in water to a.45 clear foaming solution.

(5) 280 parts of undecylimidazoline and 111 parts of alpha-glycerol-monochlorohydrin are heated, for about 1 hour, at about 140 C.-l,50 C. A-brownish liquid is obtained into which propylene oxide is introduced, drop by drop, according to Example 2, until the increase in weight amounts to 6-10 mols, per mol of the base:used. A brownish liquid is obtained which dissolves in water to a clear solution.

(6) 112 parts of undecyl-imidazoline are condensed. by'heatingat 140 c.-1eo' c., with 118 01a poiy-glycerol-chlorhydrin (content or chlorin 3%) obtained from alpha-chlorhydrin brownish liquid obtained to dissolves very easily e 21%:01dwater to an entirely clear solution.

m can pm: of hydroxy-fimQctyl-tetrahydropyrimidine (obtained from the fa 140 6.460 0., converted into the N bnzy- The product is then treated. at 120 (L-' 0., with ethylene oxide or propylene oxide, until the in- 70 crease in weight amounts to 12-15 mols of alblene'oxide, per moi of the base.

(8) Phenom-acetic acid is, in known manner, condensed with ethyleneto form the corresponding imidaaoline. OO parts or phenoxy- 7s "aromatic nucleus,

phenoxy-methylimidazolines. The solubility in water is the same.

t and O--(R0)H wherein a denotes an all-- phatic radical and n is a whole number greater selected from the group consisting of aliphatichydrocarbon radicals and aliphatic hydrocarbon "radicals substituted by hydroxy groups, said imidazolines containing a radical selected from the group consisting of than 1.

2. Imidazolines substituted in 2-position by a ber greater than 1.

- number greater than 1.

radical containing from 11 to 17 carbon atoms selected from the group consisting of aliphatic hydrocarbon radicals. and aliphatic hydrocarbon radicals substituted by hydroxy groups and containing in l-position the group (,R1O) 3-H wherein R1 denotes an aliphatic hydrocarbon radical and n is a whole number greater than 1.

3. Imidazolines substituted in 2-position by a radical containing from 11 to 17 carbon atoms selected irom the group consisting of aliphatic hydrocarbon radicals and aliphatic hydrocarbon radicals substituted by hydroxy oups and substituted in the imino group of the nucleus by the -group -(C2HAO)1;H wherein n is a whole num- 4. Imidazolines substituted in 2.-position by alkyl radicals containing from 11 to 17 carbon atoms and substituted in theimino group of the nucleus by the group -(C2H40 n-H wherein n is a whole number greater than 1.

5. Imidazolines substituted in 2-position by a radical containing from 11 to 1'7 carbon atoms selected from the group consistingof aliphatic hydrocarbon radicals and aliphatic hydrocarbon radicals substituted by hydroxy groups and substituted in l-pos'ition by organic radicals containing a member of the group consisting of AUGUST CHWALA.

Referenced by
Citing PatentFiling datePublication dateApplicantTitle
US2418077 *Aug 13, 1943Mar 25, 1947Monsanto Chemicals1, 2-disubstituted-4, 5-dihydroimidazoles
US2669546 *Dec 23, 1949Feb 16, 1954Alrose Chemical CompanyDetergents containing imidazoline lactates
US2800487 *Dec 31, 1952Jul 23, 1957Universal Oil Prod CoPolyoxyalkylene substituted heterocyclic amines and their ammonium salt derivatives
US2846440 *Dec 12, 1955Aug 5, 1958Citics Service Res And Dev ComComposition for and method of inhibiting corrosion of metals
US2940927 *Dec 12, 1955Jun 14, 1960Cities Service Res & Dev CoComposition for and method of inhibiting corrosion of metals
US2950246 *Feb 1, 1956Aug 23, 1960Cities Service Res & Dev CoProcess for increasing the permeability of oil bearing chalk formations
US2987514 *Mar 3, 1958Jun 6, 1961Petrolite CorpPolyesters
US3014864 *Dec 28, 1959Dec 26, 1961Petrolite CorpProcess of inhibiting corrosion
US3017352 *Jan 25, 1960Jan 16, 1962Petrolite CorpProcess of inhibiting corrosion
US3041338 *Jul 21, 1958Jun 26, 1962Nalco Chemical Co5-hydroxy substituted tetrahydro-pyrimidines
US3195332 *May 8, 1961Jul 20, 1965Atlas Chem IndAluminum hot rolling processes using aqueous lubricant compositions
US3216957 *Aug 14, 1962Nov 9, 1965Union Carbide CorpAntistatic thermoplastic vinyl resin compositions comprising oxyalkylated imidazolines
US3231580 *Jun 30, 1961Jan 25, 1966Hans S MannheimerSubstituted imidazolines
US3522175 *Jan 14, 1969Jul 28, 1970Kao CorpLubricant composition for synthetic fibers
US4006093 *Dec 6, 1974Feb 1, 1977Basf AktiengesellschaftSurfactants containing iodine
US4161594 *Jan 17, 1975Jul 17, 1979Ciba-Geigy AgDialcohols
US4227005 *Oct 31, 1978Oct 7, 1980Ciba-Geigy AgDialcohols
US4233451 *Oct 20, 1978Nov 11, 1980The Procter & Gamble CompanyProcess for making imidazolinium salts
US5530137 *Sep 16, 1994Jun 25, 1996Betz Paperchem, Inc.Methods and compositions for stabilizing fatty acid imidazoline solutions
US6372918 *Jun 30, 2000Apr 16, 2002Clariant GmbhCompound for inhibiting corrosion
USB530303 *Dec 6, 1974Mar 23, 1976 Title not available
DE1011580B *Nov 10, 1954Jul 4, 1957Ciba GeigyKationaktive Haarwaschmittel
U.S. Classification548/350.1, 544/298, 548/349.1, 510/500
International ClassificationC07D233/22, C07D233/16, C07D233/14
Cooperative ClassificationC07D233/22, C07D233/16, C07D233/14
European ClassificationC07D233/14, C07D233/16, C07D233/22